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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 3
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Original Articles

Alkyl Phenols from Pyrylium Salts: A Reexamination

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Pages 195-203 | Published online: 05 Dec 2006

References

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  • Details on this optimization procedure can be obtained on request
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  • The given experimental conditions can be used for other tertiaryalcohols: thus the treatment of 2-Me-2-butanol by Ac2O in HC104 medium affords a mixture of 2,6-diMe-4-Et-pyrylium salt (6) and 2,3,4,5-tetraMethyl-pyrylium salt (7) in 89% yield. 7/6+7 = 88%. Treatment of the reaction mixture by NaOH gives three isomeric phenols (60% from the alcohol): 2,3,5-triMe-phenol 8, 3,4,5-triMe-phenol 9 and 3-Et-5-Me-phenol 10. The selectivities are: 8+9/8+9+10 = 90% and 8/8+9 = 69%
  • Phenols 4 and 5 can be obtained from the petroleum ether phase by preparative GLC
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